10 Must-Stop Attractions for the Best Route 66 Road Trip

A Route 66 road trip is the ideal cross-country travel experience. Here are the best attractions you need to see along the way.

Joliet & Wilmington

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My husband, daughter, and I started our Route 66 road trip along State Route 53 in Joliet. This Chicago suburb is well known to fans of The Blues Brothers, a 1980 movie that was filmed in the area. Look up as you drive by Rich & Creamy, a retro ice cream stand within Route 66 Park, to see Jake and Elwood performing for customers. The nearby Joliet Area Historical Museum features a Route 66 Welcome Center with interactive exhibits. And the ornate Rialto Square Theatre also turns 90 this year. Make sure to stop in nearby Wilmington to see the Gemini Giant, the first of several huge “Giant Men” aka “Muffler Men” advertising statues you’ll see along Route 66. Just down the road, fuel up with burgers, cheese fries and malts at the Polk-A-Dot Drive-In, which opened in 1956. Here are the most iconic adventures in the United States.

Gardner

Photos by Lori and Dirk Vanover/Country Magazine

One of the most fun and interesting small towns we passed through is Gardner. You don’t want to miss taking a photo in the two-cell jail; it was built in 1906 to house wanderers who hopped off the passing trains. Next door to the jail you will find the Streetcar Diner. An authentic horse-drawn streetcar was brought to town in 1932 to serve as a restaurant. It is no longer open for dining service, but you can peek inside to see the vintage interior. The Riviera Roadhouse, which was built in 1928 and once hosted movie stars like Gene Kelly and Tom Mix, burned down in 2010.

Dwight & Odell

Photos by Lori and Dirk Vanover/Country Magazine

During the 1930s, oil companies often designed gas stations to look like homes so they would blend in with their suburban neighborhoods. The homey cottage feel of Ambler’s Texaco Gas Station in Dwight gives travelers a warm welcome. In Odell, the Standard Oil station is another fine example. Car traffic became so heavy in Odell during the 1930s and ’40s that children and churchgoers could not safely cross the road. A pedestrian tunnel was built under Route 66; remnants of it still exist at St. Paul Catholic Church.

Pontiac

Photos by Lori and Dirk Vanover/Country Magazine

Just before you drive into Pontiac on your Route 66 road trip, look for the Meramec Caverns barn, an early example of highway advertising painted on the side of barns. Park your car downtown and take a walking tour to see more than 20 painted murals. Also stop by the Route 66 Hall of Fame and Museum, housed in an old firehouse. It has an impressive collection of artifacts, including the “road yacht” RV and Volkswagen bus that belonged to artist Bob Waldmire, who was the inspiration for Fillmore in the Disney/Pixar movie Cars. As you exit Pontiac, observe the former State Police District 6 headquarters. Built in 1941, the distinct pistol-shaped building features Art Moderne styling. These are the states with the best American road trips.

Funks Grove & McLean

Photos by Lori and Dirk Vanover/Country Magazine

When you see the towering maple trees, you’ve arrived in Funks Grove. Pick up a bottle of maple sirup (always spelled this way), cooked by the Funks since 1824. Before you leave town, pass by the depot and country store. Dixie Truckers Home in McLean is America’s oldest truck stop, operated by one family from 1928 to 2003. Two men rented part of a mechanic’s garage to sell food to truckers. It grew into a restaurant with cabins and still serves travelers today.

Atlanta

Photos by Lori and Dirk Vanover/Country Magazine

This charming historic town, like Pontiac, features many painted murals worth admiring. Route 66 Park, a fenced-in grassy area with local history exhibits, anchors downtown. Across the street, you’ll find a lovely stone octagonal public library and clock tower, which date to the early 1900s. Also of note: The J.H. Hawes Grain Elevator and Museum and another “Giant Man,” the Bunyon Giant holding a hot dog. Stop in for a home-cooked meal at The Palms Grill Café, which offers an authentic look back at dining out during 1934. Here are the things you must check on your car before your next road trip.

Lincoln

Photos by Lori and Dirk Vanover/Country Magazine

Our nation’s 16th president christened the town in 1853 with watermelon juice. Lincoln is home to the 24-foot-high Railsplitter Covered Wagon, with Honest Abe himself in the driver’s seat. The Guinness World Records book named this amusing roadside attraction the largest covered wagon in the world. Also of note is The Mill restaurant, once famous for its fried Austrian schnitzel. The barn-red building is closed now, but it may soon become a museum.

Springfield

Photos by Lori and Dirk Vanover

Route 66 takes you straight through the downtown of the Ilinois state capital. Pay a visit to the Maid-Rite Sandwich Shop, which opened in the 1920s. Known for its loose-ground-meat sandwiches, it claims to have the nation’s first drive-thru window. Head south to the Cozy Dog Drive-In. Artist Bob Waldmire’s father, Ed, and his descendants have cooked batter-dipped hot dogs on a stick on the Mother Road since 1949. The restaurant is filled with Route 66 memorabilia. Nearby Lauterbach Tire & Auto Service features Illinois’ third “Giant Man” holding an American flag. Then head toward Auburn on State Route 4; this was Route 66 in its earliest days, from 1926 until 1930, when Route 66 was rerouted. Now, as you wind through the rural farm fields, you’ll drive along 1.5 miles of well-preserved red brick road on your Route 66 road trip.

Litchfield

Photos by Lori and Dirk Vanover/Country Magazine

In 1930 the road shifted east, going south toward Litchfield, speeding up traffic and bypassing many small towns. This foreshadowed a transition toward fast-paced interstate travel. Litchfield is home to the Sky View Drive-In, which opened in 1950. It’s Illinois’ last original operating drive-in theater along Route 66. The Ariston Café is believed to be the oldest restaurant along the historic road. Originally located in Carlinville, Ariston relocated here in 1929 to follow the rerouted road, making it a great addition to your Route 66 road trip. The restaurant moved one last time in 1935, across the street to its current location. Next door, an eye-catching neon sign for Suhling’s gas station points the way to the Litchfield Museum & Route 66 Welcome Center.

Staunton & Livingston

Photos by Lori and Dirk Vanover/Country Magazine

Next we hopped on down to Staunton, home of Henry’s Rabbit Ranch. Owner Rich Henry has a passion for pet rabbits and Volkswagens, and you’ll find plenty of both here. A modern replica that’s equal parts old-time filling station and vintage Route 66 gift shop, the ranch welcomes visitors who enjoy the quirky side of life. Keep an eye out for the “Hare It Is” sign and giant rabbit statue, a clever wink at the iconic Jack Rabbit Trading Post near Joseph City, Arizona. Our Route 66 road trip ended in Livingston. The Pink Elephant Antique Mall is a must-see, eclectic collection of statues and structures, including a fourth “Giant Man” in a Harley-Davidson shirt, a 1950s-style Twistee Treat diner and ice cream parlor, a rare 1960s-era Futuro “UFO” House, and, of course, an enormous bright pink elephant. Next, be sure to check out this road trip survival guide before you hit the open road.